m-Chloroperbenzoic acid → HCID 57971141, compound

HRID 1890496Notes

Reaction equation

HRID 1890496 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH3:12][S:13]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][N:21]=[C:20]([S:24][CH3:25])[N:19]=1)(=[O:15])=[O:14]>C(Cl)Cl.C(OCC)(=O)C>[CH3:12][S:13]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][N:21]=[C:20]([S:24]([CH3:25])=[O:6])[N:19]=1)(=[O:14])=[O:15]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 57971150HCID 57971150, compound

Product 1

HCID 57971141HCID 57971141, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

m-Chloroperoxybenzoic acid (75%, 2.4 g, 10 mmol) was added to a solution of 4-methanesulfonyloxymethyl-2-methylthiopyrimidine (2.4 g, 10 mmol, Reference Compound No. 8-2) in anhydrous methylene chloride (30 mL) and the mixture was stirred for 15 minutes under ice-cooling. m-Chloroperoxybenzoic acid (0.29 g, 1.3 mmol) was added thereto and the whole was stirred for 10 minutes under ice-cooling. The reaction mixture was diluted with ethyl acetate (100 mL), washed twice with saturated aqueous sodium hydrogencarbonate solution (30 mL), and then washed with brine (30 mL). The aqueous layer was extracted twice with chloroform (100 mL), then the extract was mixed with the ethyl acetate layer, and the whole was dried over anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure to give 2.2 g of the title Reference Compound as a colorless oil (Yield: 88%).

Workup

  1. temperaturecooling
  2. stirringthe whole was stirred for 10 minutes under ice-
  3. temperaturecooling
  4. washwashed twice with saturated aqueous sodium hydrogencarbonate solution (30 mL)
  5. washwashed with brine (30 mL)
  6. extractionThe aqueous layer was extracted twice with chloroform (100 mL)
  7. additionthe extract was mixed with the ethyl acetate layer
  8. dry with materialthe whole was dried over anhydrous magnesium sulfate
  9. concentrationThe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-06bc5d1384354afbbda682ac3d79fa11
Source dataset
uspto-grants-2013_08
Patent number
US08507485B2

Reaction notes

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